Multi-step reaction with 11 steps
1.1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide / 2.5 h / 0 °C / Inert atmosphere
2.1: triphenylphosphine hydrobromide / dichloromethane; water / 13.97 h / 0 - 20 °C
3.1: sodium acetate; pyridinium chlorochromate / dichloromethane / 1.5 h / 20 °C / Molecular sieve; Inert atmosphere
4.1: lithium trimethylsilylacetylenide / tetrahydrofuran; hexane / 0.88 h / -78 °C / Inert atmosphere
5.1: pyridine hydrogenfluoride / tetrahydrofuran / 4.8 h / -5 °C
6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 9.6 h / 20 °C / Inert atmosphere
7.1: zinc(II) chloride / tetrahydrofuran; diethyl ether / 0.25 h / -78 °C / Inert atmosphere
7.2: 0.75 h / -78 °C / Inert atmosphere
8.1: trifluoroacetic acid / diethyl ether / 10 h / 0 °C
9.1: pyridine hydrogenfluoride / tetrahydrofuran / 0 °C
10.1: tributylphosphine / acetonitrile / -40 °C / Inert atmosphere
11.1: triethylamine / diethyl ether / 0.5 h / 0 °C / Inert atmosphere
11.2: 0.83 h / -5 °C / Inert atmosphere
With
tributylphosphine; lithium trimethylsilylacetylenide; sodium acetate; triphenylphosphine hydrobromide; tetra-(n-butyl)ammonium iodide; sodium hydride; pyridine hydrogenfluoride; triethylamine; pyridinium chlorochromate; trifluoroacetic acid; zinc(II) chloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ol2028256